Effect of the structure of dietary epoxylignan on its cytotoxic activity: relationship between the structure and the activity of 7,7′-epoxylignan and the introduction of apoptosis by caspase 3/7
We compared the cytotoxic activities of dietary epoxylignans and their stereoisomers and found (−)-verrucosin, which is (7S,7′R,8R,8′R)-7,7′-epoxylignan, to be the most cytotoxic epoxylignan against HeLa cells (IC50 = 6.6 μM). On the other hand, the activity was about a factor of 10 less against HL-60. In this research on the relationship between the structure and cytotoxic activity of (−)-verrucosin 13, the 7-(4-methoxyphenyl)-7′-(3,4-dimethoxyphenyl) derivative 60, for which the activity (IC50 = 2.4 μM) is three times greater than (−)-verrucosin 13, was discovered. The induction of apoptosis by caspase 3/7 was observed upon treatment with the (−)-verrucosin derivative.
3′,4,4′-Trimethoxy-7,7′-epoxylignan showed highest IC50 value (2.4 μM) in this structure–cytotoxic activity relationship experiment of 7,7′-epoxylignan. The IC50 value of natural (−)-verrucosin was 6.6 μM.